We propose a longitudinal study to comprehensively examine how mothers' insecure states of mind in the Adult Attachment Interview (AAI) create risk for adolescent children. The sample of 13-year-old adolescents and their mothers will be recruited from an ongoing longitudinal study of Head Start children and from lists of school children qualifying for federally assisted lunch programs. We hypothesize mothers' insecure states of mind increases their reactivity to stressful situations and leaves them and their offspring vulnerable to problems in adaptation. Biological correlates of AAI status will be used to determine whether insecure states of mind are accompanied by dysregulation of the stress sensitive hypothalamic-pituitary-adrenocortical (HPA) system. Psychosocial correlates of AAI status will be assessed with standardized measures of cognitive function, dissociative symptoms, and personality. We will then test our intergenerational transmission hypothesis by considering how mothers' insecure states of mind influence children's trajectories toward increased psychiatric and problem behaviors during early adolescence. Adolescent adaptation will be comprehensively assessed with respect to salient developmental tasks (peer relationships, school/job achievement, autonomous attachment), problem behaviors (substance abuse, delinquency, and unprotected sexual activity) and emotional difficulties (internalizing, extemalizing, and dissociative symptoms) at ages 13, 14 and 15. We use a contextual risk model to specify factors that may moderate and mediate intergenerational transmission of attachment. This model identifies both family level factors (family instability and family emotional climate) and mother-teen relationship variables (harsh parenting, monitoring, and parent-teen communication) as risk factors for child problems. In addition, we will use our Head Start sub-sample to examine how maternal AAI status is associated with the child's developmental history based upon assessments of mother-child interaction at ages 4-5 and child symptoms at ages 4-5, 6-7, 8-9 and 10- 11.